#------------------------------------------------------------------------------
#$Date: 2025-11-29 21:43:29 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303772 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/95/7719519.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7719519
loop_
_publ_author_name
'Chalkidis, Savvas G.'
'Tsoureas, Nikolaos'
'Nolan, Steven P.'
'Vougioukalakis, Georgios C.'
_publ_section_title
;
 A straightforward approach to robust thiazolylidene gold complexes:
 efficient catalysts for propargylamide cycloisomerizations.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14659
_journal_page_last               14663
_journal_paper_doi               10.1039/d5dt02258d
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C11 H17 Au Cl N S'
_chemical_formula_sum            'C11 H17 Au Cl N S'
_chemical_formula_weight         427.73
_chemical_name_common            2j
_chemical_name_systematic        2j
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-08-10
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-08-11 deposited with the CCDC.	2025-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4777(6)
_cell_length_b                   7.5333(3)
_cell_length_c                   10.4391(3)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.274
_cell_measurement_theta_min      2.472
_cell_volume                     1295.82(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS Inc, 2016)'
_computing_data_collection       'APEX5 (Bruker AXS Inc, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8-Venture with Photon-III'
_diffrn_measurement_method       '/f and /w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25215
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         2.472
_exptl_absorpt_coefficient_mu    11.689
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1404 before and 0.0650 after correction.
The Ratio of minimum to maximum transmission is 0.5522.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.192
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2, n-C5H12'
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.066
_refine_diff_density_max         1.042
_refine_diff_density_min         -1.463
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0172
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0121P)²+1.4456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0367
_refine_ls_wR_factor_ref         0.0377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1550
_reflns_number_total             1694
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt02258d2.cif
_cod_data_source_block           2j
_cod_depositor_comments
'Adding full bibliography for 7719511--7719521.cif.'
_cod_database_code               7719519
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.513
_shelx_estimated_absorpt_t_min   0.321
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H4A(0.5) H4B(0.5) H4C(0.5) H5A(0.5) H5B(0.5) H5C(0.5)
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C8(H8A,H8B)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Au1 Au 0.80554(2) 0.750000 0.25354(2) 0.01356(5) Uani 1 2 d S T P . .
S1 S 0.80083(4) 0.750000 0.56040(7) 0.01735(16) Uani 1 2 d S T P . .
Cl1 Cl 0.87482(5) 0.750000 0.06415(7) 0.02086(16) Uani 1 2 d S T P . .
C1 C 0.74802(18) 0.750000 0.4208(3) 0.0150(6) Uani 1 2 d S T P . .
N1 N 0.66814(16) 0.750000 0.4482(2) 0.0142(5) Uani 1 2 d S T P . .
C7 C 0.60721(14) 0.5821(3) 0.26695(19) 0.0160(4) Uani 1 1 d . . . . .
H7A H 0.602363 0.476493 0.322846 0.019 Uiso 1 1 calc R U . . .
H7B H 0.659986 0.575698 0.221850 0.019 Uiso 1 1 calc R U . . .
C6 C 0.60388(18) 0.750000 0.3481(3) 0.0129(5) Uani 1 2 d S T P . .
H6 H 0.550406 0.749997 0.393383 0.015 Uiso 1 2 calc R U P . .
C2 C 0.64859(18) 0.750000 0.5791(3) 0.0141(6) Uani 1 2 d S T P . .
C4 C 0.7186(2) 0.750000 0.7987(3) 0.0191(6) Uani 1 2 d S T P . .
H4A H 0.680941 0.660862 0.832468 0.029 Uiso 0.5 1 calc R U P A -1
H4B H 0.703402 0.867527 0.831008 0.029 Uiso 0.5 1 calc R U P A -1
H4C H 0.773927 0.721611 0.826422 0.029 Uiso 0.5 1 calc R U P A -1
C9 C 0.5408(2) 0.750000 0.0865(3) 0.0225(7) Uani 1 2 d S T P . .
H9A H 0.494020 0.749999 0.026907 0.027 Uiso 1 2 calc R U P . .
H9B H 0.591119 0.750000 0.034779 0.027 Uiso 1 2 calc R U P . .
C3 C 0.7149(2) 0.750000 0.6555(3) 0.0156(6) Uani 1 2 d S T P . .
C5 C 0.56273(19) 0.750000 0.6232(3) 0.0194(7) Uani 1 2 d S T P . .
H5A H 0.537251 0.863363 0.600808 0.029 Uiso 0.5 1 calc R U P B -1
H5B H 0.561109 0.733861 0.716348 0.029 Uiso 0.5 1 calc R U P B -1
H5C H 0.533291 0.652776 0.581628 0.029 Uiso 0.5 1 calc R U P B -1
C8 C 0.53807(14) 0.5830(3) 0.1691(2) 0.0198(4) Uani 1 1 d . . . . .
H8A H 0.542508 0.476875 0.113549 0.024 Uiso 1 1 calc R U . . .
H8B H 0.485402 0.577133 0.214522 0.024 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Au1 Cl1 178.48(9) . . ?
C1 S1 C3 94.16(15) . . ?
S1 C1 Au1 120.67(17) . . ?
N1 C1 Au1 130.7(2) . . ?
N1 C1 S1 108.6(2) . . ?
C1 N1 C6 123.1(2) . . ?
C1 N1 C2 115.5(3) . . ?
C2 N1 C6 121.4(2) . . ?
H7A C7 H7B 108.2 . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C6 C7 C8 109.93(19) . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
N1 C6 C7 111.41(16) . . ?
N1 C6 C7 111.41(16) . 7_575 ?
N1 C6 H6 107.1 . . ?
C7 C6 C7 112.3(2) 7_575 . ?
C7 C6 H6 107.1 7_575 . ?
C7 C6 H6 107.1 . . ?
N1 C2 C5 121.3(3) . . ?
C3 C2 N1 112.9(3) . . ?
C3 C2 C5 125.8(3) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H9A C9 H9B 108.0 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 7_575 . ?
C8 C9 H9B 109.4 7_575 . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C8 111.1(3) . 7_575 ?
C2 C3 S1 108.8(2) . . ?
C2 C3 C4 128.5(3) . . ?
C4 C3 S1 122.7(2) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 C7 111.0(2) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Au1 Cl1 2.2830(7) . ?
Au1 C1 1.987(3) . ?
S1 C1 1.697(3) . ?
S1 C3 1.729(3) . ?
C1 N1 1.347(4) . ?
N1 C6 1.488(4) . ?
N1 C2 1.403(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.523(3) . ?
C7 C8 1.530(3) . ?
C6 H6 1.0000 . ?
C2 C3 1.352(4) . ?
C2 C5 1.488(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C3 1.497(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.526(3) . ?
C9 C8 1.526(3) 7_575 ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Au1 C1 N1 C6 0.000(0) . . . . ?
Au1 C1 N1 C2 180.000(0) . . . . ?
S1 C1 N1 C6 180.000(0) . . . . ?
S1 C1 N1 C2 0.000(0) . . . . ?
C1 S1 C3 C2 0.000(0) . . . . ?
C1 S1 C3 C4 180.000(0) . . . . ?
C1 N1 C6 C7 63.11(17) . . . . ?
C1 N1 C6 C7 -63.11(17) . . . 7_575 ?
C1 N1 C2 C3 0.000(1) . . . . ?
C1 N1 C2 C5 180.000(0) . . . . ?
N1 C2 C3 S1 0.000(0) . . . . ?
N1 C2 C3 C4 180.000(1) . . . . ?
C6 N1 C2 C3 180.000(0) . . . . ?
C6 N1 C2 C5 0.000(0) . . . . ?
C6 C7 C8 C9 55.9(3) . . . . ?
C2 N1 C6 C7 116.89(17) . . . 7_575 ?
C2 N1 C6 C7 -116.89(17) . . . . ?
C3 S1 C1 Au1 180.000(0) . . . . ?
C3 S1 C1 N1 0.000(0) . . . . ?
C5 C2 C3 S1 180.000(0) . . . . ?
C5 C2 C3 C4 0.000(1) . . . . ?
C8 C7 C6 N1 177.5(2) . . . . ?
C8 C7 C6 C7 -56.7(3) . . . 7_575 ?
C8 C9 C8 C7 -56.4(3) 7_575 . . . ?
